Fmoc-D-norleucine

Base Information

• Chemical Name: Fmoc-D-norleucine
• CAS No.: 112883-41-7
• Molecular Formula: C21H23NO4
• Molecular Weight: 353.418
• Hs Code.: 2924 29 70
• DSSTox Substance ID: DTXSID20373243
• Nikkaji Number: J1.882.595C
• Wikidata: Q72478739
• Mol file: 112883-41-7.mol

Synonyms:Fmoc-D-Nle-OH;Fmoc-D-norleucine;112883-41-7;(2R)-2-(9H-fluoren-9-ylmethoxycarbonylamino)hexanoic acid;(R)-2-((((9H-Fluoren-9-yl)methoxy)carbonyl)amino)hexanoic acid;D-Norleucine, N-[(9H-fluoren-9-ylmethoxy)carbonyl]-;MFCD00155639;Fmoc-D-2-aminocaproic acid;SCHEMBL7420121;DTXSID20373243;VCFCFPNRQDANPN-LJQANCHMSA-N;Fmoc-D-Nle-OH, >=98.0%;AKOS015918292;AM82589;CS-W008273;HY-W008273;AS-19000;EN300-624037;A802682;J-300349;N-alpha-(9-Fluorenylmethyloxycarbonyl)-D-norleucine;Z1982491153;(R)-2-(9H-Fluorene-9-ylmethoxycarbonylamino)hexanoic acid;(R)-2-(((9H-fluoren-9-yl)methoxy)carbonylamino)hexanoic acid;(2R)-2-({[(9H-fluoren-9-yl)methoxy]carbonyl}amino)hexanoic acid

Chemical Property of Fmoc-D-norleucine

Chemical Property:

• Appearance/Colour: White powder
• Vapor Pressure: 1.25E-13mmHg at 25°C
• Refractive Index: 1.584
• Boiling Point: 565.6 °C at 760 mmHg
• PKA: 3.91±0.21(Predicted)
• Flash Point: 295.9 °C
• PSA: 75.63000
• Density: 1.209 g/cm³
• LogP: 4.55940
• Storage Temp.: 2-8°C
• XLogP3: 4.5
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 8
• Exact Mass: 353.16270821
• Heavy Atom Count: 26
• Complexity: 472

Purity/Quality:

99% ^*data from raw suppliers

Fmoc-d-nle-oh ^*data from reagent suppliers

Safty Information:

• Safety Statements: 22-24/25

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CCCCC(C(=O)O)NC(=O)OCC1C2=CC=CC=C2C3=CC=CC=C13
• Isomeric SMILES: CCCC[C@H](C(=O)O)NC(=O)OCC1C2=CC=CC=C2C3=CC=CC=C13

Technology Process of Fmoc-D-norleucine

There total 6 articles about Fmoc-D-norleucine which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 71.0%

D-norleucine (327-56-0) + (fluorenylmethoxy)carbonyl chloride (28920-43-6) → (R)-((9H-fluoren-9-yl)methoxy)carbonyl-D-norleucine (112883-41-7,144701-20-2)

Guidance literature:

With sodium carbonate; In 1,4-dioxane; water; at 0 - 20 ℃; for 2h; Inert atmosphere;

DOI:10.1002/chem.202002449

Reference yield: 70.0%

(9H-fluoren-9-yl)methyl-((3R)-1,2-dihydroxyheptan-3-yl)carbamate → (R)-((9H-fluoren-9-yl)methoxy)carbonyl-D-norleucine (112883-41-7,144701-20-2)

Guidance literature:

(9H-fluoren-9-yl)methyl-((3R)-1,2-dihydroxyheptan-3-yl)carbamate; With sodium periodate; In tetrahydrofuran; water; at 20 ℃; for 2h; Inert atmosphere;

With sodium chlorite; potassium dihydrogenphosphate; In tetrahydrofuran; water; tert-butyl alcohol; at 20 ℃; for 1.5h; Inert atmosphere;

DOI:10.1002/chem.202002449

Reference yield:

Fmoc-norleucine (144701-20-2) → Fmoc-(S)-2-aminohexanoic acid (77284-32-3,144701-20-2) + (R)-((9H-fluoren-9-yl)methoxy)carbonyl-D-norleucine (112883-41-7,144701-20-2)

Guidance literature:

With trifluoroacetic acid; In hexane; isopropyl alcohol; at 25 ℃; Reagent/catalyst; Resolution of racemate;

DOI:10.1002/bkcs.11694

upstream raw materials:

(fluorenylmethoxy)carbonyl chloride

Fmoc-norleucine

2-amino-hexanoic acid

D-norleucine

Downstream raw materials:

benzyl (2S,5R,8R)-2-allyl-3,6-diaza-5-(3-([(3,4-dihydro-2,2,5,7,8-pentamethyl-2H-1-benzopyran-6-yl)sulfonyl]guanidino)propyl)-4,7-dioxo-8-(9H-9-fluorenylmethoxycarboxamido)dodecanoate

Refernces

• 1、 Islam, Md. Fokhrul,Adhikari, Suraj,Paik, Man-Jeong,Lee, Wonjae. "Determination of Chemical and Enantiomeric Purity of α-Amino Acids and their Methyl Esters as N-Fluorenylmethoxycarbonyl Derivatives Using Amylose-derived Chiral Stationary Phases". . p. 332 - 338. Retrieved 2019/04/13.